Product Design Lead
2 - 5 years
Charlotte, NC
Full-time
Onsite
1 month ago
About the role
About the Role
We are looking for a Product Design Lead to lead our product design team at Olly Olly. This is a player-coach leadership role — you are responsible for design outcomes, not just design output. You will spend the majority of your time managing and elevating the work of your team, with roughly 20-30% of your time contributing directly as a designer yourself on high-priority work.
Design at Olly Olly should be practical, fast, and thoughtful. We want someone who sees AI as part of the design workflow — not a side tool — and who can help the team use LLMs and prototyping tools to move faster, think more clearly, and test ideas earlier, while still maintaining a high bar for craft, usability, and clarity.
You will report to our CPO and work in close partnership with engineering and product to ensure great design ships — not just great mockups.
Three Direct Reports
What You Will Own
How You Will Spend Your Time
What Success Looks Like
What We Are Looking For
Nice to Have
About Olly Olly
We are a $25M ARR company helping thousands of home service businesses get found, get calls, and grow. Design is central to how we deliver value — both in our product and how we show up in the market. This is an opportunity to own a small but high-impact design team at a company that is scaling fast and investing in getting the product right.
Portfolio Required
We are looking for a Product Design Lead to lead our product design team at Olly Olly. This is a player-coach leadership role — you are responsible for design outcomes, not just design output. You will spend the majority of your time managing and elevating the work of your team, with roughly 20-30% of your time contributing directly as a designer yourself on high-priority work.
Design at Olly Olly should be practical, fast, and thoughtful. We want someone who sees AI as part of the design workflow — not a side tool — and who can help the team use LLMs and prototyping tools to move faster, think more clearly, and test ideas earlier, while still maintaining a high bar for craft, usability, and clarity.
You will report to our CPO and work in close partnership with engineering and product to ensure great design ships — not just great mockups.
Three Direct Reports
- UX/UI Product Designer (in-app)
- UX/UI Product Designer (in-app)
- UI/Web Designer (marketing and brand-adjacent)
What You Will Own
- Day-to-day management of a three-person design team — running design reviews, unblocking work, giving direct feedback, and raising the bar on quality
- The design system and visual language for our core product, ensuring consistency across every screen and interaction
- UX flows, wireframes, and prototypes for new features — from early problem definition through to production-ready specs
- Design QA — making sure what gets built matches what was designed
- Improving how product, design, and engineering work together — ensuring design is involved early in problem definition, not just UI delivery
- Collaboration with engineering and product on sprint planning, roadmap prioritization, and tradeoff decisions
- Darko's output across UI and web — reviewing his work and ensuring brand and product design stay visually coherent
- A culture of prototyping and early validation — pushing the team to test ideas before they are fully built
How You Will Spend Your Time
- 60-70% — Managing the team: reviews, feedback, career development, process improvement, and cross-functional coordination
- 20-30% — Hands-on design: contributing directly to high-priority or complex features where your execution adds the most value
What Success Looks Like
- Design is involved earlier and more effectively in product development
- Product experiences become more intuitive, cohesive, and outcome-oriented
- The team ships faster with better alignment across product, design, and engineering
- Design quality rises across the product — not just within isolated features
- The design team becomes a force multiplier for product strategy and execution
What We Are Looking For
- 6+ years of product design experience, with at least 1-2 years managing or formally leading other designers
- An exceptional eye for design — your taste shows up in your portfolio, your feedback, and the standards you hold your team to
- Strong product thinking — you understand user flows, information architecture, and how design decisions connect to business outcomes
- Experience designing and shipping B2B SaaS or workflow-heavy products
- Experience building or maintaining a design system in a fast-moving product environment
- Proven ability to ship — you have a track record of moving work from concept to production without losing quality
- Active use of AI tools such as Claude, ChatGPT, Cursor, or similar in your design workflow
- Fluency in Figma and modern design tooling
- Strong communicator who can translate design decisions into business rationale for non-design stakeholders
- Comfortable in a growth-stage environment where priorities shift and you need to make good decisions with incomplete information
Nice to Have
- Experience designing for SMB audiences or home services markets
- Background in SaaS or digital marketing platforms
- Familiarity with web and marketing design in addition to product
About Olly Olly
We are a $25M ARR company helping thousands of home service businesses get found, get calls, and grow. Design is central to how we deliver value — both in our product and how we show up in the market. This is an opportunity to own a small but high-impact design team at a company that is scaling fast and investing in getting the product right.
Portfolio Required
- Please include a portfolio with your application. Applications without one will not be considered.
- We want to see product design work — UX flows, shipped features, design systems — not just visual polish.
- Show us your thinking, not just the final output.
Skills
Advertising Services